Search Cheap Flights to
Chester

Photo by Elizabeth Massa Peroulakis

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Chester Flights as Low as $84

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Spirit Airlines
Thu, May 1 - Tue, May 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$84 Roundtrip, found 3 days ago
$84
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, May 1 from Orlando Intl. to Bradley Intl., returning Tue, May 6, priced at $84 found 3 days ago
Spirit Airlines
Thu, May 1 - Tue, May 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$92 Roundtrip, found 3 days ago
$92
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, May 1 from Orlando Intl. to Bradley Intl., returning Tue, May 6, priced at $92 found 3 days ago
Frontier Airlines
Thu, May 1 - Tue, May 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$93 Roundtrip, found 3 days ago
$93
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Thu, May 1 from Orlando Intl. to Bradley Intl., returning Tue, May 6, priced at $93 found 3 days ago
JetBlue Airways
Thu, May 8 - Mon, May 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$95 Roundtrip, found 1 day ago
$95
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, May 8 from Orlando Intl. to Bradley Intl., returning Mon, May 12, priced at $95 found 1 day ago
Frontier Airlines
Sat, May 3 - Wed, May 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$102 Roundtrip, found 3 days ago
$102
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 3 from Orlando Intl. to Bradley Intl., returning Wed, May 7, priced at $102 found 3 days ago
Spirit Airlines
Thu, May 1 - Tue, May 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$105 Roundtrip, found 3 days ago
$105
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Thu, May 1 from Orlando Intl. to Bradley Intl., returning Tue, May 6, priced at $105 found 3 days ago
Frontier Airlines
Sat, May 3 - Sun, May 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$108 Roundtrip, found 3 days ago
$108
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 3 from Orlando Intl. to Bradley Intl., returning Sun, May 4, priced at $108 found 3 days ago
Breeze Airways
Wed, May 28 - Sun, Jun 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$109 Roundtrip, found 2 days ago
$109
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, May 28 from Orlando Intl. to Bradley Intl., returning Sun, Jun 1, priced at $109 found 2 days ago
Breeze Airways
Wed, May 28 - Sun, Jun 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$111 Roundtrip, found 2 days ago
$111
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, May 28 from Orlando Intl. to Bradley Intl., returning Sun, Jun 1, priced at $111 found 2 days ago
American Airlines
Sat, Jul 19 - Tue, Jul 22
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$145 Roundtrip, found 4 days ago
$145
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sat, Jul 19 from Charlotte-Douglas Intl. to Bradley Intl., returning Tue, Jul 22, priced at $145 found 4 days ago
Spirit Airlines
Thu, May 22 - Thu, May 29
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$193 Roundtrip, found 5 days ago
$193
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Thu, May 22 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Thu, May 29, priced at $193 found 5 days ago
Delta
Sat, Jul 19 - Tue, Jul 22
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Jul 19 from Charlotte-Douglas Intl. to Bradley Intl., returning Tue, Jul 22, priced at $197 found 4 days ago
Bargain Flight
Fri, Sep 19 - Mon, Sep 22
SAV
Savannah - Hilton Head Intl.
BDL
Bradley Intl.
$231 Roundtrip, found 8 hours ago
$231
Roundtrip
found 8 hours ago
Select Bargain Flight flight, departing Fri, Sep 19 from Savannah - Hilton Head Intl. to Bradley Intl., returning Mon, Sep 22, priced at $231 found 8 hours ago
Delta
Wed, May 14 - Sat, May 24
ROA
Roanoke Regional
BDL
Bradley Intl.
$246 Roundtrip, found 4 days ago
$246
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, May 14 from Roanoke Regional to Bradley Intl., returning Sat, May 24, priced at $246 found 4 days ago
Frontier Airlines
Mon, Apr 21 - Fri, Apr 25
BWI
Baltimore Washington Intl. Thurgood Marshall
BDL
Bradley Intl.
$295 Roundtrip, found 1 day ago
$295
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Apr 21 from Baltimore Washington Intl. Thurgood Marshall to Bradley Intl., returning Fri, Apr 25, priced at $295 found 1 day ago
United
Tue, Apr 22 - Thu, May 1
CHO
Charlottesville-Albemarle
BDL
Bradley Intl.
$344 Roundtrip, found 5 hours ago
$344
Roundtrip
found 5 hours ago
Select United flight, departing Tue, Apr 22 from Charlottesville-Albemarle to Bradley Intl., returning Thu, May 1, priced at $344 found 5 hours ago

Cheap Flights to Chester

Fall in love at first flight with your vacation to Chester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CEF airport.

What is the cheapest month to fly to Chester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chester are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 15 to choose from for your flight to Chester.

What airport is best to fly into Chester?

When you’re planning your trip to Chester, convenience is the name of the game. Luckily, Chester Barnes Municipal Airport is nearby so you can deplane and get going on checking off everything on your Chester must-do list.

How much are flights to Chester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $84, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chester?

The trick to saving a stack of cash on your flight to Chester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $84 right now, why wait?

Chester Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$83

Last Minute Hotel Deals in Chester

D. Hotel Suites & Spa
D. Hotel Suites & Spa
3 out of 5
1 Country Club Rd, Holyoke, MA
The price is $141 per night from Apr 27 to Apr 28
$141
includes taxes & fees
Apr 27 - Apr 28
Stay at this 3-star spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ...
9.2/10 Wonderful! (2,301 reviews)
"Great accommodations the pool was very nice and the staff was exceptional"

Reviewed on Apr 16, 2025

D. Hotel Suites & Spa
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is $119 per night from May 4 to May 5
$119
includes taxes & fees
May 4 - May 5
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (558 reviews)
"The hotel is cozy and charming. The rooms are well-appointed. The staff was great. Easy check-in, check-out. The bar is well stocked and they offer free (real) coffee in the morning!"

Reviewed on Apr 14, 2025

Life House Berkshires
Quality Inn West Springfield
Quality Inn West Springfield
2.5 out of 5
1150 Riverdale St, West Springfield, MA
The price is $94 per night from May 11 to May 12
$94
includes taxes & fees
May 11 - May 12
Book a stay at this golf hotel in West Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,000 reviews)
"It was ok"

Reviewed on Apr 7, 2025

Quality Inn West Springfield
La Quinta Inn & Suites by Wyndham Springfield MA
La Quinta Inn & Suites by Wyndham Springfield MA
3 out of 5
100 Congress Street, Springfield, MA
The price is $127 per night from Apr 30 to May 1
$127
includes taxes & fees
Apr 30 - May 1
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
8/10 Very Good! (1,283 reviews)
"Love it!"

Reviewed on Apr 16, 2025

La Quinta Inn & Suites by Wyndham Springfield MA
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
The price is $108 per night from Apr 28 to Apr 29
$108
includes taxes & fees
Apr 28 - Apr 29
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,001 reviews)
"This place was being remodeled and had I known I would have stayed elsewhere."

Reviewed on Apr 16, 2025

The Yankee, Trademark Collection by Wyndham
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 out of 5
190 Meadow Street, South Lee, MA
The price is $134 per night from Apr 28 to Apr 29
$134
includes taxes & fees
Apr 28 - Apr 29
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (620 reviews)
"Great deal for villa resort suite. Lots of space, great condition, great amenities, great location."

Reviewed on Apr 12, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
The Ellery
The Ellery
3.5 out of 5
259 Elm Street, Northampton, MA
The price is $155 per night from May 4 to May 5
$155
includes taxes & fees
May 4 - May 5
Stay at this 3.5-star B&B in Northampton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (657 reviews)
"The staff were very friendly. Breakfast was healthy. There are delicious chocolate chip cookies."

Reviewed on Apr 12, 2025

The Ellery
Tru by Hilton Chicopee Springfield
Tru by Hilton Chicopee Springfield
2.5 out of 5
440 Memorial Dr, Chicopee, MA
The price is $129 per night from Apr 28 to Apr 29
$129
includes taxes & fees
Apr 28 - Apr 29
Stay at this hotel in Chicopee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,008 reviews)
"We've stayed here a few times and this time I need some extras due to recovering from a foot surgery. The staff was absolutely wonderful and accommodating with my need for extra pillows to elevate my foot, and delivered it to our room within minutes. If you're staying in Chicopee, stay at the ..."

Reviewed on Apr 15, 2025

Tru by Hilton Chicopee Springfield
See all 803 properties in Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.